


If At First You Don't Succeed...

by destieldrabblesdaily



Category: Supernatural
Genre: AU, Friends to Lovers, Happy Ending, M/M, Misunderstandings, Roommates, Sam x Jess in the background
Language: English
Status: Completed
Published: 2016-01-19
Updated: 2016-01-19
Packaged: 2018-05-15 00:34:47
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,768
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5764915
Author URL: https://archiveofourown.org/users/destieldrabblesdaily/pseuds/destieldrabblesdaily
Summary: <blockquote class="userstuff">
              <p>For the prompt: “Wait, did you just flirt with me?" <br/>"Have been for the past year, but thanks for noticing.”</p>
<p>Dean has a huge crush on his friend Castiel, with whom he also shares an apartment. When he decides that he finally wants to woo Cas, everything that could possibly go wrong, does indeed go wrong.</p>
            </blockquote>





	If At First You Don't Succeed...

**~ January ~**

“Perfect.”

Dean mumbled some praise to himself as he lit the maroon colored candle in the center of the table. Not to brag, but he’d done a great job here; matching maroon napkins, crystal wineglasses that he’d borrowed from his colleague Pamela, a silver candle holder… And hey, he was even using the fancy grey plates for once, not those ugly orange monstrosities with yellow ducks on them that his roommate Cas had insisted on buying.

Speaking of Cas, the guy was running late, tonight of all nights. Then again, Cas often worked late on Fridays, so Dean should’ve seen that coming. The suspense was killing him all the same.

Attempting to chase away his nerves, Dean distracted himself with checking the casserole in the oven one last time. _Awesome._ Looking good, smelling even better.

Wooing Cas would be a piece of cake, and the best part? This way, Dean wouldn’t have to talk about ‘feelings’. He would show instead of tell, letting Castiel know that he wanted to be more than friends, doing so with a nice, romantic gesture. Dean Winchester would come, see, and conquer. Possibly not in that order, if everything went according to plan.

He spent another thirty minutes pacing the apartment back and forth, occasionally staring out of the window, watching the early January snow as it fell.

Just as it was starting to get dark outside, in walked Cas. Snowflakes were clinging to both his black trench coat and the dark chaos that was his hair. Cas shuddered as he took off his coat, but he smiled broadly the second he spotted Dean, who was forlornly standing there in the middle of the living room, anxiously shuffling his feet.

“Hello, Dean.” Castiel greeted, still completely oblivious to what was about to go down.

Dean cleared his throat, his stomach turning. This was it, _show time_.

“Heya, Cas…” He responded hesitantly. “I ehm… I made dinner.”

Cas nodded as he put down his briefcase, still smiling. “You usually do on Fridays, Dean.” He pointed out matter-of-factly. “But it goes without saying that I very much appreciate your cooking skills.”

“Right…” Dean muttered, rubbing his sweaty hands against his jeans. _Dammit_. “I just mean…”

Dean trailed off, gesturing to the other end of the room,  waving his hand at the table for two that he’d set, obviously meant for a candlelit dinner.

Blue eyes curiously assessed the situation, and Cas’ mouth suddenly formed a big ‘O’.

“I see…” Castiel replied with a tentative head tilt. “You seem nervous, but I understand now, you have a _date._ Don’t worry, I will make myself scarce, you don’t have to feel bad about wanting the place to yourself for a night.”

Before Dean could object or even correct Cas, the guy was already putting his coat back on and grabbing his keys, calling a last “good luck, Dean” over his shoulder before he closed the door behind him with a soft ‘click’.

Pouting, Dean stared at the traces of melting snow on the floor; the only thing that Cas had left behind.

He breathed a dejected “thanks” for good measure. In the kitchen, a timer started beeping obnoxiously, signaling that the casserole was ready. _Peachy._

***

**~ May ~**

Dean’s hands were clutching his own knees as he dutifully stared at the screen, glad that it was impossible for anyone to see him blush in the dark theatre. Cas was sitting right beside him, their shoulders nearly touching.

After giving it some thought, Dean had picked the scariest movie there was, so that hopefully it would give him an excuse to grab Cas’ arm. Or Cas’ hand. Or well… _any_ part of Cas really.

Naturally, when Dean had suggested to go to the movies together, Cas had asked why their friends Charlie and Benny weren’t tagging along like they usually did. At Dean’s brilliant reply _-“just because, Cas”-_ Castiel had given him that puzzled look that was so adorably Cas, but thankfully he’d shrugged and agreed anyway.

Despite Dean’s effort, now that they were here, Dean was too terrified to even cast a sideways glance at his friend, let alone touch the guy.  Dean tapped his feet, fumbled with his clothes, slurped his soda, but otherwise didn’t dare to make a move.

That all changed when they made it to the last ten minutes of the movie. Surprisingly, things got creepy as hell for the first time in eighty minutes, and Dean reached for his friend without even thinking about it at first. His heart was wildly pounding in his chest once he realized what he was doing, both because of the movie and the bold move that he was making on Cas.

Dean held his breath, eyes glued to the screen, only to feel the tips of his fingers brush against… The empty paper container in Cas’ lap.

_Son of a bitch_. He’d missed his target.

Horrified, he turned his head, meeting blue eyes that were watching him apologetically.

“I apologize, Dean… I ate all the popcorn. I didn’t know you still wanted some, I would’ve shared.”

While Dean was still racking his brain for a useful reply, the ending credits were already rolling by. Lights were turned on, and Cas was getting up from his seat, glancing down at Dean expectantly.

“Are you coming?”

Dean forced back a sigh, bleakly staring at the empty popcorn container in Cas’ hands.

“Yeah, Cas… Yeah, let’s get out of here.”

***

**~ July ~**

Dean grinned to himself as he inhaled the smell of the salty sea, summer, and fresh air. This beach vacation had been the best idea in the history of ever; they could all use a break. Not too far away, Dean’s younger brother Sam and his fiancé Jessica were chasing each other, water splashing everywhere, the sun playing with Jess’ long blonde curls.

Even closer, there was Cas, sitting on a large fluffy towel that he’d spread out on the sand, enjoying the sunny weather while reading a book, his back to Dean.

Dean’s heartbeat picked up as he stared down at the three different ice cream cones that he’d just scored. He swallowed his nerves, walking to the edge of the water to systematically hand one to Sam -hazelnut of course-, and to pass a strawberry flavored one to Jess.

His feet turned heavy as he left the two lovebirds behind with their sugary goodness, aiming for Castiel with a mission.

Cas lifted his head as soon as Dean approached, blue eyes making Dean melt even faster than the ice cream that he was about to use as his bargaining chip.

“Hey Cas… I thought that the two of us could… _share_ this? Only if you want to, it’s chocolate.”

After about fifteen failed attempts, Dean knew that he was due for a win here. Surely Cas had to know what sharing this ice cream cone would imply. Dean was counting the seconds as he waited for Cas to say something, anything at all.

And then Cas frowned, quizzically lifting an eyebrow at Dean.

“You know that I’m lactose intolerant, Dean… I’m allergic to most types of ice cream.” There was a brief pause as Dean mentally beat himself up over his rookie mistake, but Cas’ chuckle cut through the silence. “Ah, I see… You were joking about sharing because you know I can’t have ice cream. It’s alright, I don’t mind you having some. What kind of friend would I be if I made you feel guilty about something like that, you should enjoy.”

A single genuine smile, and within a matter of seconds, Cas was back to reading. Dean stared at the ice cream cone that was crushed between his fingers, cursing himself to the fiery pits of hell. He felt too nauseous to eat the chocolaty treat himself, and so he ended up dumping his failed plan in the nearest trash can.

Maybe it was time to accept that he and Cas were doomed, at least as anything other than best friends…

***

**~ October ~**

The morning sun, filtered through the leaves, painted the local park in orange, red, and yellow. Dean couldn’t put his finger on why Fall was his favorite season, but it definitely was. He suspected that Cas agreed.

Castiel was sitting next to Dean on the bench, a notebook in his lap. Dean watched, fascinated as Castiel’s clever hand moved the pencil across the paper, saving images of the trees, the leaves, the pond nearby. They sipped hot chocolate from cheap paper cups while Castiel sketched, Dean watching his friend in awe.

Being here, doing this, made Dean feel happy and depressed at the same time. Because this was so much more than an ordinary crush, there was no way to dismiss that.

The way Cas’ eyes were shining. A stray leaf landing on top of Cas’ head, the orange standing out against dark brown. Cas’ tongue poking out slightly as he concentrated on his drawing. Dean didn’t just want to go out with Cas, Dean was _in love_.

The thought had barely crossed his mind, when Cas suddenly gazed up at him, adding a fresh shade of blue to a swirl of orange.

“It’s beautiful, isn’t it?” Cas asked casually, nodding at the scenery surrounding them.

“Yeah…” Dean answered, scratching the back of his neck; a nervous habit. “Nowhere near as beautiful as you though.”

Holy shit, no… _What the hell?_ Where did this word vomit come from? Dean snapped his mouth shut, even knowing that it was way too late for that.

Cas observed him, brow furrowed, eyes wide. After what felt like a lifetime, Cas’ expression softened, his face relaxing as if he’d suddenly seen the light.

“Wait… Did you just _flirt_ with me, Dean?”

Dean released a puff of air, figuring that it was too late to take any of it back anyway. Cas had heard him, loud and clear.

“Have been for the past year, Cas.” He admitted, followed by a hysterical snort. “But thanks for noticing.”

***

**~ December ~**

They were back at that same bench, freezing their asses off. Cas’ sketches were worth it; he wanted to capture the first snow, and Dean was a supportive boyfriend. In between strokes of his pencil, Cas pressed chaste, warm kisses against Dean’s jaw as a reward. Dean’s arms were wrapped around Cas’ waist, keeping Castiel warm.

After a while, snowflakes started falling again. Castiel kept drawing, and Dean Winchester was very pleased with himself as he kissed the top of Cas’ head. Who cared that he sucked at flirting? At the end of the day, he still got the guy.

**Author's Note:**

> For more Destiel stories, go to destieldrabblesdaily.tumblr.com


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